Cleveland Brown and Cleveland Jr. leave Quahog and take to the road. On their way to California, they stop in Cleveland's hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Cleveland, still in love with Donna, is determined to start a new life with her, even if Donna's kids aren't exactly angels.

After Cleveland has "the talk" with Roberta, Cleveland Jr. becomes scared and takes a vow of chastity. Meanwhile, Rallo becomes a church greeter.

Cleveland celebrates his first Thanksgiving with his new family and discovers a surprising secret about Donna's Auntie Momma.

Cleveland and Donna are excited to have the house to themselves when Cleveland Jr. and Roberta go on a school trip to Washington, D.C., but a disgruntled Rallo will do whatever it takes to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.

In order to teach her an important lesson, Roberta's new teacher encourages her to alter her appearance. Unbeknownst to him, Cleveland Jr. befriends, and falls in love wit the disguised Roberta.

Roberta and Rallo have a surprise for Lacey, Roberta’s wealthy rival. Meanwhile, Cleveland Junior learns responsibility while working at The Stool, but when he starts making changes to the guys’ hangout, a feud erupts between father and son.

Cleveland and Donna get mugged at an ATM and Cleveland gets shot, and the media makes it seem as if he was a hero. Meanwhile, Roberta convinces Rallo that she might be dying of a terrible disease and makes him do her bidding.

Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams; Cleveland Jr. challenges her boyfriend to a rap battle.

Cleveland and Cleveland Jr. teach Donna and the kids their tradition of celebrating Black History Month. However, when Rallo learns about his heritage at school, he provokes Cleveland into a battle royale with neighbor, Lester.

Cleveland takes a struggling rapper (Kanye West) under his wing and, together, they write and record a new hit single.

"How Do You Solve a Problem Like Roberta?" is the eleventh episode of the second season of the American animated television sitcom The Cleveland Show. It aired on Fox in the United States on January 16, 2011. The episode had guest appearances by Wilmer Valderrama and cast members of the show Glee.

In this episode, After Cleveland criticizes her parenting skills, Donna lets him deal with Roberta by himself. This episode came in third with 5.5 million viewers beating American Dad! and Bob's Burgers.

When Lester invests in Cleveland's beer truck business and loses his life savings, he is so upset that he decides to take his own life - or does he? Meanwhile, Rallo is tired of getting his hair cut by his mom and opens his own barbershop in the kitchen.

When Cleveland is reunited with his former high school classmate, "Fatty Patty," who is now skinny, beautiful and still has a crush on Cleveland, Donna becomes extremely jealous and wary of Patty's motives for wanting to be friends with Cleveland. Patty turns out to be a little crazy, and after she tries to steal Cleveland's "essence," Donna goes on the hunt to stop her.